18 days in Italy & Greece Itinerary

Created using Klarna Trips Europe trip planner
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Fly
1
Como, Italy
— 1 night
Drive
2
Cinque Terre, Italy
— 1 night
Train
3
Pisa, Italy
— 1 night
Drive
4
Florence, Italy
— 3 nights
Drive
5
Siena, Italy
— 1 night
Fly to Santorini, Bus to Kamari
6
Kamari, Greece
— 2 nights
Bus to Santorini, Fly to Athens
7
Athens, Greece
— 1 night
Fly
8
Vasilikos, Greece
— 6 nights
Fly

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Como, Italy — 1 night

City of Silk

Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
On the 5th (Fri), take in the spiritual surroundings of Basilica di San Fedele, take in the architecture and atmosphere at Cathedral of Como (Duomo), then look for gifts at Peter Ci Abbigliamento, then admire the natural beauty at I Giardini di Villa Melzi, and finally pause for some serene contemplation at Basilica di San Giacomo. On the next day, explore the galleries of Villa Carlotta, admire the landmark architecture of Villa del Balbianello, and then admire the striking features of Villa Olmo.

For reviews, maps, and tourist information, use the Como trip itinerary builder app.

Toronto, Canada to Como is an approximately 11.5-hour flight. You'll lose 6 hours traveling from Toronto to Como due to the time zone difference. In May in Como, expect temperatures between 25°C during the day and 13°C at night. Finish your sightseeing early on the 6th (Sat) so you can drive to Cinque Terre.
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Parks · Historic Sites · Museums · Shopping
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Cinque Terre, Italy — 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 7th (Sun): get into the urban bustle at Vernazza, stroll through Footpath Monterosso - Vernazza, explore the historical opulence of Castello Doria, then take a tour by water with Enjoy Cinqueterre Boat Tours, and finally explore the historical opulence of Castello di Riomaggiore.

To see ratings, where to stay, more things to do, and more tourist information, you can read our Cinque Terre itinerary builder.

Traveling by car from Como to Cinque Terre takes 3.5 hours. Alternatively, you can take a train. Expect a daytime high around 25°C in May, and nighttime lows around 13°C. Finish your sightseeing early on the 7th (Sun) so you can take a train to Pisa.
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Pisa, Italy — 1 night

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 8th (Mon), admire the striking features of St Martin Cathedral, get to know the fascinating history of Knights’ Square, enjoy breathtaking views from Leaning Tower of Pisa, make a trip to Piazza dei Miracoli, then take in the spiritual surroundings of Duomo di Pisa, and finally stroll the grounds of Camposanto.

Start your trip to Pisa by creating a personalized itinerary on Klarna Trips.

Traveling by train from Cinque Terre to Pisa takes 2 hours. Alternatively, you can drive. In May, daytime highs in Pisa are 25°C, while nighttime lows are 13°C. Finish up your sightseeing early on the 8th (Mon) so you can go by car to Florence.
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Florence, Italy — 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, take in the views from Ponte Vecchio, and appreciate the extensive heritage of Piazza del Duomo.

To see more things to do, ratings, traveler tips, and tourist information, refer to the Florence online travel route planner.

Getting from Pisa to Florence by car takes about 1.5 hours. Other options: take a bus; or take a train. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Cap off your sightseeing on the 11th (Thu) early enough to go by car to Siena.
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Siena, Italy — 1 night

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 12th (Fri): make a trip to Centro Storico di Siena and then take in the architecture and atmosphere at Duomo di Siena.

To see reviews, more things to do, traveler tips, and other tourist information, use the Siena trip maker site.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Wrap up your sightseeing by early afternoon on the 12th (Fri) to allow time for travel to Kamari.
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Kamari, Greece — 2 nights

Kamari is a coastal village on the southeastern part of the Aegean island of Santorini, Greece, in the Cyclades archipelago with a population of approx. Start off your visit on the 13th (Sat): delve into the distant past at Ancient Thera, then learn about winemaking at Gaia Winery, then delve into the distant past at Akrotiri, and finally kick back and relax at Kamari Beach. Get ready for a full day of sightseeing on the next day: hike along Ekklisia Theoskepasti hiking trail, contemplate the waterfront views at Amoudi Bay, and then make a trip to Sunset in Oia.

To see where to stay, photos, reviews, and more tourist information, use the Kamari travel route builder tool.

Getting from Siena to Kamari by combination of flight and bus takes about 9 hours. Other options: do a combination of train, flight, and bus; or do a combination of car and ferry. The time zone difference moving from Central European Standard Time to Eastern European Standard Time is 1 hour. Traveling from Siena in May, plan for somewhat warmer nights in Kamari, with lows around 20°C. Finish your sightseeing early on the 14th (Sun) so you can travel to Athens.
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Athens, Greece — 1 night

The Birthplace of Democracy

One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.
Start off your visit on the 15th (Mon): stop by Plaka, then take an in-depth tour of Acropolis Museum, and then delve into the distant past at Acropolis of Athens.

To find photos, ratings, traveler tips, and tourist information, you can read our Athens itinerary planner.

Do a combination of bus and flight from Kamari to Athens in 4 hours. Alternatively, you can do a combination of ferry and taxi; or ride a ferry. May in Athens sees daily highs of 29°C and lows of 20°C at night. Wrap up your sightseeing on the 15th (Mon) early enough to fly to Vasilikos.
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Historic Sites · Neighborhoods · Museums
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Vasilikos, Greece — 6 nights

Home to just a few hundred year-round residents, Vasilikos draws thousands of daily visitors with its beaches and restaurants during peak tourist season.
You'll find plenty of places to visit near Vasilikos: Tsilivi (Planos) (Speed Boats Tours & Tsilivi Waterpark), Blue Caves (in Korithi) and Navagio Beach (Shipwreck Beach) (in Anafonitria). And it doesn't end there: kick back and relax at Vasilikos Beach, stop by Razi Aroma, pause for some serene contemplation at Church Agios Nikolaos of Molos, and head off the coast to Marathonisi.

To find more things to do, other places to visit, reviews, and tourist information, go to the Vasilikos sightseeing website.

Getting from Athens to Vasilikos by flight takes about 2.5 hours. Other options: do a combination of bus and taxi. Traveling from Athens in May, expect slightly colder with lows of 16°C in Vasilikos. You will have some time to spend on the 21st (Sun) before leaving for home.
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Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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Tuscany travel guide

4.4
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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Greece travel guide

4.3
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.
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